Process for the preparation of 4-haloalkylnicotinonitriles
AssigneeAventis CropScience GmbH
InventorsSergiy Pazenok, Henricus Maria Martinus Bastiaans
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Abstract
4-Haloalkylnicotinonitriles having the formula (I) which are suitable as intermediates in the preparation of pesticides, are obtained by: (a) reacting a 3-amino-1-haloalkyl-2-propen-1-one RF—C(O)—CH═CH—NH2 (II) in a condensation reaction with a compound of the formula (III) to (VII), (R1Z)CH═CH—CN (III) (R1Z)2CH—CH2—CN (IV) Hal-CH═CH—CN (V) Hal2CH—CH2CN (VI) HC≡C—CN (VII), to give a compound of the formula (VIII), (IX) and/or (X), RF—C(O)—CH═CH—NH—CH═CH—CN (VIII) RF—C(O)—CH═CH—NH—CH(ZR1)—CH2—CN (IX) RF—C(O)—CH═CH—NH—CH(Hal)—CH2—CN (X), wherein RF is (C1-C4)-haloalkyl, R1 is alkyl, Hal is Cl or Br and each Z, independently, is O, S, NR1 or OCO; and (b) subjecting the reaction product to a ring closure reaction.
Claims6
A compound having the formula (VIII), (IX) or (X):
- RF—C(O)—CH═CH—NH—CH═CH—CN (VIII)
- RF—C(O)—CH═CH—NH—CH(ZR1)—CH2—CN (IX)
- RF—C(O)—CH═CH—NH—CH(Hal)—CH2—CN (X)
- wherein:
- RF is (C1-C4)-haloalkyl;
- R1 is an alkyl group;
- Z is O, S or OCO and
- Hal is Cl or Br.
Dependencies are inferred from the claim text.